| UTR Pro Tennis Series Zadar | 2021/11/19 13:50 | Ivan Penev v Alexander Lazov | 6-3,3-6,3-6 |
| UTR Pro Tennis Series Zadar | 2021/11/16 10:30 | Ivan Penev v Oleksii Osadchyi | 6-1,6-1 |
| UTR Pro Tennis Series Zadar | 2021/11/15 13:30 | Ivan Penev v Vladan Tadic | 4-6,6-4,0-6 |
| UTR Pro Tennis Series Zadar | 2021/11/14 12:00 | Alen Rogic-Hadzalic v Ivan Penev | 6-3,4-6,6-2 |
| ITF M15 Sozopol | 2021/10/11 09:00 | Ivan Penev v Berk Ilkel | 6-7,6-1,8-10 |
| ITF M15 Sozopol | 2021/10/10 09:00 | Ivan Penev v Gianluca Coloma-Heck | 6-1,6-3 |
| ITF M15 Sozopol | 2021/10/04 07:00 | Yann Wojcik v Ivan Penev | 3-6,7-5,10-2 |
| ITF M15 Sozopol | 2021/09/13 10:30 | Tommaso Compagnucci v Ivan Penev | 6-2,6-3 |
| ITF M15 Bagnoles-de-l'Orne | 2022/01/13 13:15 | Hugo Pierre v Jurgen Briand | 1-6,3-6 |
| ITF M15 Bagnoles-de-l'Orne | 2022/01/11 17:00 | Hugo Pierre v Alexander Wolfschmidt | 6-1,7-5 |
| ITF M15 Monastir | 2021/12/15 09:30 | Hugo Pierre v Aziz Ouakaa | 1-6,1-6 |
| ITF M15 Monastir | 2021/12/08 13:40 | Viktor Jovic v Hugo Pierre | 6-3,6-3 |
| ITF M15 Monastir | 2021/12/06 14:30 | Hugo Pierre v Olivier Rojas | 2-6,1-6 |
| ITF M15 Monastir | 2021/12/06 08:00 | Hugo Pierre v Maxence Rivet | 6-1,6-1 |
| ITF M15 Monastir | 2021/12/05 09:00 | Hugo Pierre v Maceo Simpson | 6-3,7-5 |
| ITF M15 Monastir | 2021/11/30 08:00 | Kasidit Samrej v Hugo Pierre | 6-2,2-6,6-4 |